EP0786675B1 - Brillenglas - Google Patents

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Publication number
EP0786675B1
EP0786675B1 EP19970300271 EP97300271A EP0786675B1 EP 0786675 B1 EP0786675 B1 EP 0786675B1 EP 19970300271 EP19970300271 EP 19970300271 EP 97300271 A EP97300271 A EP 97300271A EP 0786675 B1 EP0786675 B1 EP 0786675B1
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EP
European Patent Office
Prior art keywords
lens
spectacle lens
ultraviolet absorber
benzotriazole
wavelength
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Revoked
Application number
EP19970300271
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English (en)
French (fr)
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EP0786675A2 (de
EP0786675A3 (de
Inventor
Hironori c/o Teijin Chemicals Ltd. Yamashita
Tsuneo c/o Teijin Chemicals Ltd. Shimada
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Teijin Ltd
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Teijin Chemicals Ltd
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Publication of EP0786675A3 publication Critical patent/EP0786675A3/de
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Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472—Five-membered rings
    • C08K5/3475—Five-membered rings condensed with carbocyclic rings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y10T428/263—Coating layer not in excess of 5 mils thick or equivalent
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31507—Of polycarbonate

Definitions

  • This invention relates to a spectacle lens which has excellent impact resistance and transparency and high ultraviolet light absorbing power, particularly absorbing power for ultraviolet light having a specific wavelength. More specifically, it relates to a spectacle lens which comprises a polycarbonate resin as a resin component, almost free from yellowing, and has excellent workability.
  • a polycarbonate resin has excellent characteristic properties such as high refractive index, transparency and impact resistance and has been recently attracting much attention as a material for a lens, particularly as a material for a spectacle lens. Since a spectacle lens formed from a polycarbonate resin is thinner, lighter and has much higher impact strength than the conventional glass lenses and plastic lenses manufactured by casting polymerization (to be referred to as "cast lenses” hereinafter) it is safe and exhibits high functionality. Therefore, it has been and is used as an accommodation lens, sunglasses, protective glasses and the like.
  • a polycarbonate resin itself has ultraviolet light absorbing power and moreover, since a polycarbonate resin is thermoplastic, it can contain a desired ultraviolet absorber easily when the ultraviolet absorber is blended at the time of melt-molding. Therefore, an absorber for ultraviolet light having a long wavelength can be blended into a polycarbonate resin.
  • a conventional polycarbonate resin can absorb ultraviolet light having a wavelength of up to 375 nm at the utmost. To absorb ultraviolet light having a longer wavelength exceeding 375 nm, the amount of an ultraviolet absorber to be added must be increased to 2 to 10 times that for a normal case.
  • an ultraviolet absorber Since an ultraviolet absorber has generally a sublimation property, when a large amount of the ultraviolet absorber is added, a mirror-surface mold is stained by the sublimation of the ultraviolet absorber in injection-molding of a polycarbonate resin, thereby greatly deteriorating the outer appearance of the resulting lens.
  • Japanese Patent Publication Nos. Hei 6-35141 and Hei 6-41162 disclose a method for forming a surface layer for a multi-layer laminate sheet or film at the time of extrusion molding by adding 0.1 to 20 parts by weight of an oligomer-type ultraviolet absorber which hardly sublimes into a polycarbonate resin.
  • the object of this method is to provide the sheet or film with weatherbility, and is not optical.
  • there is a type of ultraviolet absorber which has power of absorbing ultraviolet light having a long wavelength it is necessary to add a large amount of a bluing agent to erase a yellow tint, because a polycarbonate resin yellows considerably when this type of ultraviolet absorber for absorbing a long wavelength is added.
  • Japanese Laid-open Patent Application No. Hei 7-92301 proposes a plastic lens for inhibiting the transmission of ultraviolet light and near infrared light by adding an ultraviolet absorber and an infrared absorber.
  • a lens obtained by this method has unsatisfactory transparency. It has been presumed, therefore, that in a spectacle lens formed from a polycarbonate resin, complete absorption of ultraviolet light having a wavelength of 380 nm or less and high transparency conflict with each other.
  • Japanese Laid-open Patent Application No. Sho 62-146951 teaches a polycarbonate resin composition which contains 0.001 to 5 parts by weight of an alkylidenebis(benzotriazolylphenol) compound represented by a specific structural formula based on 100 parts by weight of a polycarbonate resin to improve optical resistance.
  • This publication shows the measurement result of a change in the yellowness index ( ⁇ YI) of a test piece prepared by adding 0.3 % by weight of each of five different specific compounds to a polycarbonate resin when it was irradiated with ultraviolet light from a high-pressure mercury lamp. The results merely show that the change in the yellowness index was reduced by adding the above specific compounds.
  • Japanese Laid-open Patent Application No. Hei 4-292661 teaches a resin composition containing an ultraviolet absorber which has a maximum absorption in a wavelength of 280 to 360 nm and does not absorb a wavelength of 400 nm in an amount of 0.01 to 0.15 part by weight based on 100 parts by weight of a transparent thermoplastic resin containing a polycarbonate resin.
  • This resin composition has been developed as a camera lens having a transmittance of light having a wavelength of 400 nm of 80 % or more because a silver salt film has a sensitivity peak at a wavelength of 400 nm.
  • a first object of the present invention is to provide a spectacle lens formed from a polycarbonate resin which has excellent impact resistance and transparency and can cut ultraviolet light having a specific wavelength almost completely.
  • a second object of the present invention is to provide a spectacle lens formed from a composition which is hardly yellowed by ultraviolet light and is free from the contamination of the mirror surface of a mold by the sublimation of an ultraviolet absorber during molding.
  • a third object of the present invention is to provide a spectacle lens which does not transmit a wavelength of 380 nm substantially and has high luminous transmittance.
  • the inventors of the present invention have conducted intensive studies on an ultraviolet absorber for use in a polycarbonate resin and have found that, when two different ultraviolet absorbers, each having a maximum absorption at a specific wavelength are combined and used in specific amounts and a specific ratio, ultraviolet light having a wavelength of 380 nm can be completely absorbed without deteriorating moldability and impairing the transparency of a lens.
  • the present invention has been achieved upon this finding.
  • a spectacle lens formed from a resin composition which essentially consists of:
  • the two different ultraviolet absorbers (A) and (B) are combined in the above-described amounts. Further, the weight ratio of the ultraviolet absorber (B) to the ultraviolet absorber (A) is advantageously in the range of 0.05 to 4.
  • the spectacle lens of the present invention will be described in detail hereinunder.
  • the polycarbonate resin used in the present invention is an aromatic polycarbonate resin obtained by reacting a divalent phenol and a carbonate precursor.
  • a divalent phenol is 2,2-bis(4-hydroxyphenyl)propane (generally called bisphenol A), but the divalent phenol may be other divalent phenol.
  • divalent phenol examples include bis(hydroxyaryl)alkanes such as bisphenol A, bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)octane, 2,2-bis(4-hydroxyphenyl)phenylmethane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 1,1-bis(4-hydroxy-3-tert-butylphenyl)propane, 2,2-bis(4-hydroxy-3-bromophenyl)propane, 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane and 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane; bis(hydroxyphenyl)cycloalkanes such as 1,1-bis(hydroxyphenyl)cyclopentane and 1,1-bis(hydroxypheny
  • 2,2-bis(4-hydroxyphenyl)propane (bisphenol A) is preferably used as a divalent phenol component.
  • bisphenol A 2,2-bis(4-hydroxyphenyl)propane
  • 70 mol% or more, particularly 80 mol% or more, of the whole divalent phenol component consists of bisphenol A.
  • the most preferable aromatic polycarbonate resin is obtained from a divalent phenol component substantially comprising bisphenol A.
  • phosgene as a polycarbonate precursor
  • a reaction between a divalent phenol component and phosgene is generally carried out in the presence of an acid binder and an organic solvent.
  • an acid binder an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, or an amine compound such as pyridine.
  • an organic solvent a hydrocarbon halide such as methylene chloride or chlorobenzene.
  • a catalyst such as tertiary amine or quaternary ammonium salt may be used, and a terminator such as a phenol or a alkyl-substituted phenol exemplified by p-tert-butyl phenol is preferably used as a molecular weight modifier.
  • the reaction temperature is generally 0 to 40°C, the reaction time is several minutes to 5 hours, and pH during reaction is preferably maintained at 10 or more.
  • ester exchange method melting method
  • diester carbonate as a carbonate precursor
  • a divalent phenol component and diester carbonate are stirred, under heating, in a predetermined ratio in the presence of an inert gas and the resulting alcohol or phenol is distilled off.
  • the reaction temperature differs depending on the boiling point of the produced alcohol or phenol but is generally 120 to 300°C.
  • the reaction can be carried out at a reduced pressure from the beginning while the produced alcohol or phenol is distilled off.
  • an ordinary ester exchange reaction catalyst may be used.
  • diester carbonate used for this ester exchange reaction examples include diphenyl carbonate, dinaphthyl carbonate, dimethyl carbonate, diethyl carbonate, dibutyl carbonate and the like, of which diphenyl carbonate is particularly preferred.
  • the molecular weight of the polycarbonate resin used in the present invention is preferably 17,000 to 30,000, particularly preferably 20,000 to 26,000, in terms of viscosity-average molecular weight.
  • a spectacle lens is a precision molding and it is important to transfer a mirror surface of a mold accurately so as to provide a prescribed curvature and a prescribed diopter.
  • the resin composition of the present invention comprises two kinds of ultraviolet absorbers which differ from each other in wavelength absorption characteristics in the polycarbonate resin.
  • One of the absorbers is an ultraviolet absorber (A) having a maximum absorption in a wavelength range of 300 to 345 nm and the other is an ultraviolet absorber (B) having a maximum absorption in a wavelength range of 346 to 400 nm.
  • the absorption maximums of these two ultraviolet absorbers are absorption spectra measured in a chloroform solution at a concentration of 10 mg/lit. using a 10 mm-thick quartz cell.
  • the present invention by using a combination of the above specific two ultraviolet absorbers (A) and (B), ultraviolet light having a wavelength of 380 nm can be almost completely absorbed and the luminous transmittance of 87 % or more is maintained and the resulting lens has a good hue even though the amount of each of the absorbers is small.
  • the present invention has such an advantage that the chance of yellowing with ultraviolet light is extremely small.
  • the ultraviolet absorber (A) has a maximum absorption in a wavelength of 300 to 345 nm and is selected from benzophenone-based ultraviolet absorbers typified by 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, 2-hydroxy-4-methoxy-2'-carboxybenzophenone and 2,4-dihydroxybenzophenone; and benzotriazole-based ultraviolet absorbers typified by 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-[2-hydroxy-3-(3,4,5,6-tetrahydrophthalimidemethyl)-5-methylphenyl]benzotriazole, 2-(2-hydroxy-3,5-di-tert-butylphenyl)benzotriazole and 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole. They may be used alone or in combination of two or more.
  • benzotriazole-based ultraviolet absorbers are preferred, of which 2-(2'-hydroxy-5'-methylphenyl)benzotriazole and 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole are particularly preferred.
  • the ultraviolet absorber (A) is contained in an amount of 0.05 to 0.5 part by weight based on 100 parts by weight of a polycarbonate resin. If the amount is less than 0.05 part by weight, ultraviolet absorption power will be insufficient, while if it is more than 0.5 part by weight, ultraviolet absorption power will not be improved any longer, and on the contrary, sublimation during molding occurs, the haze of the resulting lens increases and the hue of the lens deteriorates greatly.
  • the particularly preferable amount is 0.1 to 0.35 part by weight.
  • the ultraviolet absorber (B) having a maximum absorption in a wavelenght of 346 to 400 nm, which is used in combination with the ultraviolet absorber (A) is selected from benzophenone-based ultraviolet absorbers typified by 2,2'-dihydroxy-4-methoxybenzophenone; and benzotriazole-based ultraviolet absorbers typified by 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3,5-di-tert-butyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2,2'-methylenebis[4-(1,1,3,3,-tetramethylbutyl)-6-(2H-benzotriazole-2-yl)phenol], 2-[2-hydroxy-3,5-bis( ⁇ , ⁇ -dimethylbenzyl)phenyl]-2H-benzotriazole and 2-(3,5,-di-tert-amyl-2-hydroxyphenyl)benzotri
  • benzotriazole-based ultraviolet absorbers are preferred, of which 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 2,2'-methylenebis[4-(1,1,3,3,-tetramethylbutyl)-6-(2H-benzotriazole-2-yl)phenol] and 2-[2-hydroxy-3,5-bis( ⁇ , ⁇ -dimethylbenzyl)phenyl]-2H-benzotriazole are particularly preferred.
  • the ultraviolet absorber (B) is contained in an amount of 0.01 to 0.3 part by weight based on 100 parts by weight of the polycarbonate resin. If the amount is less than 0.01 part by weight, ultraviolet absorption power will be insufficient, while if it is more than 0.3 part by weight, the hue may considerably deteriorate depending on the ultraviolet absorber (B), resulting in a hazy lens.
  • the amount is more preferably 0.015 to 0.27 part by weight, particularly preferably 0.02 to 0.25 part by weight.
  • the blending ratio (weight) R of the ultraviolet absorber (B) to the ultraviolet absorber (A) represented by the equation R (B)/(A) should be set to 0.05 to 4.
  • the blending ratio R is below 0.05, ultraviolet absorption power will be insufficient, while if the blending ratio is above 4, the hue will considerably deteriorate, thereby making the produced lens unsuitable for practical use.
  • the blending ratio is particularly preferably 0.06 to 3.
  • the blending timing and blending method of the ultraviolet absorber (A) and the ultraviolet absorber (B) are not particularly limited. As for the blending timing, they may be added during or after the polymerization of the polycarbonate resin. As for the blending method, they may be mixed with the polycarbonate resin in the form of a powder, pellet or bead by an arbitrary mixer such as a tumbler, ribbon blender, high-speed mixer or the like and then, subjected to melt kneading. The ultraviolet absorber (A) and the ultraviolet absorber (B) may be added simultaneously or in a desired order.
  • the polycarbonate resin composition of the present invention may contain a mold-release agent so as to obtain a favorable result.
  • a mold-release agent is generally used a saturated aliphatic acid ester exemplified by monoglycerides such as monoglyceride stearate; lower aliphatic acid esters such as stearic acid stearate; higher aliphatic acid esters such as sebacic acid behenate; erythritol esters such as pentaerythritol tetrastearate; and the like.
  • the mold-release agent is used in an amount of 0.03 to 1 part by weight based on 100 parts by weight of the polycarbonate resin.
  • a phosphorous acid ester-based thermal stabilizer may be used in an amount of 0.001 to 0.1 part by weight based on 100 parts by weight of the polycarbonate resin as required.
  • Preferred examples of the phosphorous acid ester-based thermal stabilizer include tris(nonylphenyl)phosphite, triphenyl phosphite, tris(2,4-di-tert-butylphenyl)phosphite, tetrakis(2,4-di-tert-butylphenyl)-4,4'-biphenylene diphosphonite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol-diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol-di-phosphite, tris(ethylphenyl)phosphite, tris(butylphenyl)
  • a bluing agent may be contained in the polycarbonate resin composition of the present invention to erase a yellow tint of a lens due to the polycarbonate resin or ultraviolet absorbers, when the polycarbonate resin composition is molded into a spectacle lens. Any bluing agent may be used without a problem as far as it can be used for a polycarbonate resin.
  • An anthraquinone-based dye is generally preferred because it is easily available.
  • bluing agent examples include: color index (C.A.) No. 60725 [general name: Solvent Violet 13; trade name: "Macrolex Violet B” of Bayer AG., "Dia Resin Blue G” of Mitsubishi Chemical MKV Co., Ltd., “Sumiplast Violet B” of Sumitomo Chemical Co., Ltd.]; C.A. No. 68210 [general name: Solvent Violet 31; trade name: "Dia Resin Violet D" of Mitsubishi Chemical MKV Co., Ltd.]; C.A. No. 60725 [general name: Solvent Violet 33; trade name: "Dia Resin Blue-J" of Mitsubishi Chemical MKV Co., Ltd.); C.A. No.
  • 61500 [general name: Solvent Blue 94, trade name: "Dia Resin Blue-N" of Mitsubishi Chemical MKV Co., Ltd.]; C.A. No.68210 [general name: Solvent Violet 36; trade name: "Macrolex Violet 3R” of Bayer AG.], General name: Solvent Blue 97 [trade name: "Macrolex Blue RR” of Bayer AG.]; and C.A. No.61110 [general name: Solvent Blue 45; trade name: "Tetrazole Blue RLS" of Sandoz AG].
  • the bluing agent is blended into the polycarbonate resin in an amount of 0.3 to 1.2 ppm.
  • an accommodation spectacle lens has a thin portion and a thick portion and there is a big difference in thickness between these portions. Accordingly, the absorption of the bluing agent is strong, a hue difference will be produced between central and peripheral portions of the lens owing to the difference of the thickness, thereby greatly deteriorating the outer appearance of the lens.
  • a spectacle lens formed from the polycarbonate resin composition of the present invention has extremely excellent transparency, and a luminous transmittance of 87 % or more, preferably 88 % or more when the thickness of the lens is 1.5 mm.
  • the luminous transmittance refers to a value measured under conditions to be described hereinafter and for a lens formed from the composition of the present invention which comprises a polycarbonate resin, ultraviolet absorbers (A) and (B), phosphorus-based stabilizer, mold-release agent and bluing agent.
  • the luminous transmittance is a value obtained on the assumption that the dye or pigment is not contained.
  • the spectacle lens of the present invention has high transparency and a low yellowness index (YI).
  • the yellowness index of the lens is set at 0.7 to 1.8, preferably 1 to 1.6 when the thickness of the lens is 5 mm. If the yellowness index is below 0.7, transmitted light is bluish when the resin composition is formed into a lens, while if the yellowness index is above 1.8, the transmitted light is yellowish.
  • the polycarbonate spectacle lens Since the polycarbonate spectacle lens has a high refractive index and high impact resistance, attempts have been made to reduce the thickness and weight of the lens and a concave lens generally has a central thickness as extremely thin as about 1.5 mm. Therefore, the ultraviolet light transmittance of a 1.5 mm-thick central portion of a lens is extremely important from the standpoint of protecting eyes.
  • a polycarbonate molding material which is colored in advance may be used, and even in this case, the spectacle lens of the present invention is extremely effective because it has a great ultraviolet light absorption effect and high transparency.
  • the spectacle lens of the present invention uses a polycarbonate resin as a substrate, it has high impact strength and a high refractive index and is excellent in ultraviolet light absorption effect, particularly in the effect of absorbing harmful ultraviolet light having a wavelength of 380 to 400 nm.
  • the present invention makes it possible to provide two different types of spectacle lenses according to application and purpose: one placing stress on luminous transmittance and the other placing stress on ultraviolet light absorption power.
  • the amount of the ultraviolet absorber (A) used be selected from the range of 0.1 to 0.5 part by weight and that of the ultraviolet absorber (B) from the range of 0.01 to 0.1 part by weight based on 100 parts by weight of the polycarbonate resin and the blending weight ratio R of the ultraviolet absorber (B) to the ultraviolet absorber (A) be selected from the range of 0.05 to 0.5 so as to achieve a spectral transmittance for a wavelength of 380 nm of 0.005 % or less and a luminous transmittance of 88 % or more when the thickness of the lens is 1.5 mm and a yellowness index (YI) of 0.7 to 1.8 when the thickness is 5.0 mm.
  • the amount of the ultraviolet absorber (A) used be selected from the range of 0.05 to 0.5 part by weight and that of the ultraviolet absorber (B) from the range of 0.05 to 0.3 part by weight based on 100 parts by weight of the polycarbonate resin and the blending weight ratio R of the ultraviolet absorber (B) to the ultraviolet absorber (A) should be selected from the range of 0.5 to 4 so as to achieve a spectral transmittance for a wavelength of 400 nm of 10 % or less and a luminous transmittance of 87 % or more when the thickness of the lens is 1.5 mm and a yellowness index (YI) of 0.7 to 1.8 when the thickness is 5.0 mm.
  • the spectral transmittance for a wavelength of 380 nm can be 0.005 % or less.
  • a spectacle lens formed from a resin composition comprising:
  • the spectacle lens of the present invention has a spectral transmittance for 10 % or less, preferably 5 % or less, when the thickness of the lens is 1.5 mm. And, the lens has a luminous transmittance of 87 % or more, preferably 88 % or more, when the thickness is 1.5 mm, which means that the lens has extremely high transparency. Further, the lens has a yellowness index (YI) of 0.7 to 1.8, preferably 1.2 to 1.6, when the thickness is 5.0 mm.
  • YI yellowness index
  • the starting material itself of the ultraviolet absorber represented by the above general formula [1] has low yellowness index, compared with other ultraviolet absorbers for absorbing a long wavelength and hence, this composition has such an advantage that the amount of the bluing agent to be added can be reduced.
  • the ultraviolet absorber to be contained in the spectacle lens is a compound which has an APHA (hue) value of 200 or less and a molecular weight of 500 to 2,000 and is represented by the above general formula [1].
  • APHA value denotes a hue value of an absorber itself and is a hue value measured when 5 g of an ultraviolet absorber is dissolved in 100 ml of dichloromethane and the resulting solution is compared with a Harzen color number standard solution in accordance with JIS K6901 as will be described hereinafter.
  • an ultraviolet absorber having an APHA (hue) value of more than 200 When an ultraviolet absorber having an APHA (hue) value of more than 200 is used, the obtained spectacle lens has a strong yellow tint and hence, a large amount of the bluing agent is required to erase this yellow tint. When a large amount of the bluing agent is used, luminous transmittance greatly lowers with the consequence that a spectacle lens having a luminous transmittance of 87 % or more cannot be obtained.
  • An ultraviolet absorber having an APHA value of 150 or less is particularly preferred. Further, if an ultraviolet absorber represented by the above general formula [1] has a molecular weight of less than 500, it will sublime at the molding temperature or a mold temperature of the polycarbonate resin, thereby staining the mold during molding and deteriorating the outer appearance of the obtained lens.
  • the compatibility of the ultraviolet absorber with the polycarbonate resin will decrease and the haze of the lens will increase, thereby making it difficult to obtain a transparent spectacle lens.
  • a material providing a haze of 2 % or more is not suitable as a material for a spectacle lens.
  • the halogen atom represented by X is selected from chlorine, bromine, iodine and fluorine;
  • the alkyl group and aralkyl group are selected from alkyl and aralkyl groups having 1 to 20 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, secondary butyl, tertiary butyl, isobutyl, amyl, tertiary amyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, 1,1,3,3-tetramethylbutyl, nonyl, decyl, isodecyl, undecyl, dodecyl, octadecyl, benzyl, ⁇ -methylbenzyl, cumyl and the like.
  • the alkoxy group and aralkyloxy group are an alkoxy group and an aralkyloxy group derived from the above alkyl and aralkyl groups, respectively.
  • the aryl group is selected from a phenyl group and the like.
  • the aryloxy group is selected from a phenoxy group and the like.
  • the alkyl group and aralkyl group represented by R 1 and R 2 are independently selected from alkyl and aralkyl groups having 1 to 20 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, secondary butyl, tertiary butyl, isobutyl, amyl, tertiary amyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, 1,1,3,3-tetramethylbutyl, nonyl, decyl, isodecyl, undecyl, dodecyl, octadecyl, benzyl, ⁇ -methylbenzyl, cumyl and the like.
  • alkyl and aralkyl groups having 1 to 20 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, secondary but
  • Y is not particularly limited if it is a divalent organic group capable of coupling two benzotriazolylphenol groups but is preferably a divalent organic group represented by the following formula: wherein R 3 is a hydrogen atom or alkyl group, R 4 is an alkylene group or allylene group, and n and m are each an integer of 1 to 5.
  • the alkyl group represented by R 3 in the above formula is exemplified by an alkyl group having 1 to 20 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, secondary butyl, tertiary butyl, isobutyl, amyl, tertiary amyl, hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, tertiary octyl, nonyl, tertiary nonyl, decyl, undecyl and the like.
  • the alkylene group and allylene group represented by R 4 are an alkylene group having 1 to 12 carbon atoms and an allylene group having 6 to 30 carbon atoms, respectively.
  • the compound is preferably a compound in which X is a hydrogen atom, chlorine atom or methyl group, R 1 and R 2 are independently a hydrogen atom, alkyl group having 1 to 10 carbon atoms, cyclohexyl group, aralkyl group having 7 to 9 carbon atoms, phenyl group or naphthyl group, and Y is (R 3 is a hydrogen atom or alkyl group having 1 to 4 carbon atoms, m is 2, and n is 3).
  • the particularly preferable compound is a compound in which X is a hydrogen atom, R 1 and R 2 are independently a hydrogen atom, alkyl group having 1 to 9 carbon atoms or aralkyl group having 7 to 9 carbon atoms, and Y is or (R 3 is a hydrogen atom, m is 2, and n is 3).
  • An ultraviolet absorber represented by the above general formula [1] is contained in an amount of 0.5 to 3 parts by weight based on 100 parts by weight of a polycarbonate resin.
  • transmittance of ultraviolet light having a wavelength of 400 nm is 10 % or more and when the amount is more than 3 parts by weight, the transmittance is 1 % or less.
  • the amount is particularly preferably 0.5 to 2 parts by weight.
  • the ultraviolet absorber When the ultraviolet absorber is used in an amount of 0.5 to 2 parts by weight and an ultraviolet absorber for absorbing a long wavelength is further added in an amount of 0.01 to 0.07 part by weight as the case may be, the transmittance of ultraviolet light having a wavelength of 400 nm can be reduced without greatly deteriorating the hue.
  • a spectacle lens obtained from the above-described polycarbonate resin composition of the present invention can absorb harmful ultraviolet light almost completely while retaining excellent impact resistance and transparency, and is excellent in safety, effects obtained from the spectacle lens are remarkable. Further, the spectacle lens has no problem with moldability.
  • the lens had a good hue.
  • Table 1 The results are shown in Table 1.
  • a lens having an excellent ultraviolet screening property and good hue was obtained in the same manner as in Example 1 except that the amount of 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole (ultraviolet absorber (A)) added was changed to 0.3 part, that of 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole (ultraviolet absorber (B)) to 0.03 part and that of the bluing agent for making uniform a blue tint to 0.7 ppm.
  • the results are shown in Table 1.
  • a lens having an excellent ultraviolet screening property and good hue was obtained in the same manner as in Example 1 except that the amount of 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole (ultraviolet absorber (A)) added was changed to 0.15 part, that of 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole (ultraviolet absorber (B)) to 0.06 part and that of the bluing agent for making uniform a blue tint to 0.8 ppm.
  • the results are shown in Table 1.
  • a lens having an excellent ultraviolet screening property and good hue was obtained in the same manner as in Example 1 except that the amount of 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole (ultraviolet absorber (A)) added was changed to 0.3 part, 0.05 part of 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazole-2-yl)phenol] having a maximum absorption at a wavelength of 349 nm (ultraviolet absorber (B)) was used in place of 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, and the amount of the bluing agent for making uniform a blue tint was changed to 0.5 ppm.
  • Table 1 The results are shown in Table 1.
  • a lens having an excellent ultraviolet screening property and good hue was obtained in the same manner as in Example 4 except that the amount of 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole (ultraviolet absorber (A)) added was changed to 0.25 part, that of 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazole-2-yl)phenol] (ultraviolet absorber (B); B-2) to 0.08 part, and that of the bluing agent for making uniform a blue tint to 0.5 ppm.
  • the results are shown in Table 1.
  • a lens having an excellent ultraviolet screening property and good hue was obtained in the same manner as in Example 1 except that the amount of 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole (ultraviolet absorber (A)) added was changed to 0.25 part, 0.1 part of 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole and 0.05 part of 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazole-2-yl)phenol] were used as the ultraviolet absorber (B), and the amount of the bluing agent for making uniform a blue tint was changed to 0.7 ppm.
  • the spectral transmittances of 380 nm and 400 nm, luminous transmittance, YI and hue of the lens are shown in Table 2.
  • a lens having an excellent ultraviolet screening property and good hue was obtained in the same manner as in Example 6 except that the amount of 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole (ultraviolet absorber (A)) added was changed to 0.2 part and that of 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazole-2-yl)phenol] (ultraviolet absorber (B)) to 0.1 part.
  • the results are shown in Table 2.
  • a lens having an excellent ultraviolet screening property and good hue was obtained in the same manner as in Example 6 except that the amount of 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole (ultraviolet absorber (A)) added was changed to 0.2 part, that of 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazole-2-yl)phenol] (ultraviolet absorber (B)) to 0.15 part, and that of the bluing agent for making uniform a blue tint to 1 ppm.
  • Table 2 The results are shown in Table 2.
  • a lens having an excellent ultraviolet screening property and good hue was obtained in the same manner as in Example 6 except that the amount of 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole (ultraviolet absorber (A)) added was changed to 0.2 part, that of 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole (ultraviolet absorber (B)) to 0.07 part, that of 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazole-2-yl)phenol] (ultraviolet absorber (B)) to 0.15 part, and that of the bluing agent for making uniform a blue tint to 0.8 ppm.
  • Table 2 The results are shown in Table 2.
  • a lens having an excellent ultraviolet screening property and good hue was obtained in the same manner as in Example 6 except that the amount of 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole (ultraviolet absorber (B)) added was changed to 0.05 part, that of 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazole-2-yl)phenol] (ultraviolet absorber (B)) to 0.1 part, and that of the bluing agent for making uniform a blue tint to 0.7 ppm.
  • Table 2 The results are shown in Table 2.
  • a lens was obtained in the same manner as in Example 1 except that only 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole (ultraviolet absorber (A)) was used in an amount of 0.33 part, but 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole (ultraviolet absorber (B)) was not used.
  • the results are shown in Table 1. Although the lens had a good hue, it could not sufficiently absorb wavelengths of 380 nm and 400 nm.
  • a lens was obtained in the same manner as in Example 1 except that only 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole (ultraviolet absorber (B)) was used in an amount of 0.02 part, but 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole (ultraviolet absorber (A)) was not used. Although the lens had a good hue, it could not sufficiently absorb wavelengths of 380 nm and 400 nm.
  • a lens was obtained in the same manner as in Example 1 except that only 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole (ultraviolet absorber (B)) was used in an amount of 0.15 part and the amount of the bluing agent for making uniform a blue tint was changed to 1.1 ppm, but 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole (ultraviolet absorber (A)) was not used,.
  • the results are shown in Table 1.
  • the hue of the lens was dark blue and a difference was seen in the hue between central and peripheral portions of the lens.
  • a lens was obtained in the same manner as in Example 6 except that only 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole (ultraviolet absorber (A)) was used in an amount of 0.25 part, but 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole and 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazole-2-yl)phenol] (ultraviolet absorber (B)) were not used. Although the lens had a good hue, it could not sufficiently absorb wavelengths of 380 nm and 400 nm.
  • a lens was obtained in the same manner as in Example 10 except that 0.05 part of 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole and 0.1 part of 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazole-2-yl)phenol] were used as the ultraviolet absorber (B), but 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole (ultraviolet absorber (A)) was not used. Although the lens had a good hue, it could not sufficiently absorb wavelength of 380 nm.
  • a lens having an excellent ultraviolet screening property, high heat resistance and a good hue was obtained in the same manner as in Example 11 except that 0.03 part of trisnonylphenyl phosphite (compound D) was newly added as a phosphite-based compound.
  • the results are shown in Table 3.
  • a lens having an excellent ultraviolet screening property and a good hue was obtained in the same manner as in Example 13 except that the amount of the ultraviolet absorber used was changed to 1 part and that of the bluing agent for making uniform a blue tint to 0.7 ppm. The results are shown in Table 4.
  • a lens having an excellent ultraviolet screening property and a good hue was obtained in the same manner as in Example 13 except that the amount of the ultraviolet absorber used was changed to 2 parts and that of the bluing agent for making uniform a blue tint to 0.8 ppm. The results are shown in Table 4.
  • a lens having an excellent ultraviolet screening property and a good hue was obtained in the same manner as in Example 13 except that 1 part of hexane-1,6-diylbis[3-(3-benzotriazole-2-yl-5-tert-butyl-4-hydroxyphenyl)propionate](B-3)(molecular weight of 761, melting point of 118 to 120°C, APHA of 150) was used in place of the ultraviolet absorber used in Example 13 and the amount of the bluing agent for making uniform a blue tint was changed to 0.8 ppm.
  • Table 4 The results are shown in Table 4.
  • a lens having an excellent ultraviolet screening property and a good hue was obtained in the same manner as in Example 13 except that the amount of the ultraviolet absorber used was changed to 1 part, 0.02 part of 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole (molecular weight of 316, melting point of 138 to 141°C, APHA of 300) was further used as an additional ultraviolet absorber, and the amount of the bluing agent for making uniform a blue tint was changed to 1 ppm. The results are shown in Table 4.

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Claims (20)

  1. Brillenglas, erzeugt aus einer Harzzusammensetzung, welche im wesentlichen besteht aus:
    (1) 100 Gewichtsteilen eines Polycarbonat-Harzes;
    (2) 0,05 bis 0,5 Gewichtsteilen eines Ultraviolett-Absorbers (A) mit einem Absorptionsmaximum bei einer Wellenlänge von 300 bis 345 nm, wenn in einer Chloroformlösung gemessen wird; und
    (3) 0,01 bis 0,3 Gewichtsteilen eines Ultraviolett-Absorbers (B) mit einem Absorptionsmaximum bei einer Wellenlänge von 346 bis 400 nm, wenn in einer Chloroformlösung gemessen wird.
  2. Brillenglas nach Anspruch 1, wobei das Gewichtsverhältnis des Ultraviolett-Absorbers (B) zu dem Ultraviolett-Absorber (A) in dem Bereich von 0,05 bis 4 bezüglich des Gewichtsverhältnisses von (B)/(A) liegt.
  3. Brillenglas nach Anspruch 1, welches eine Spektraldurchlässigkeit für eine Wellenlänge von 380 nm von 0,005% oder weniger aufweist, wenn die Dicke des Glases 1,5 mm beträgt.
  4. Brillenglas nach Anspruch 1, welches eine Spektraldurchlässigkeit für eine Wellenlänge von 400 nm von 70% oder weniger aufweist, wenn die Dicke des Glases 1,5 mm beträgt.
  5. Brillenglas nach Anspruch 1, welches eine Spektraldurchlässigkeit für eine Wellenlänge von 380 nm von 0,005% oder weniger und eine Spektraldurchlässigkeit für eine Wellenlänge von 400 nm von 70% oder weniger aufweist, wenn die Dicke des Glases 1,5 mm beträgt.
  6. Brillenglas nach Anspruch 1, welches eine Spektraldurchlässigkeit für eine Wellenlänge von 400 nm von 10% oder weniger aufweist, wenn die Dicke des Glases 1,5 mm beträgt.
  7. Brillenglas nach Anspruch 1, welches eine Spektraldurchlässigkeit für eine Wellenlänge von 380 nm von 0,005% oder weniger und eine Spektraldurchlässigkeit für eine Wellenlänge von 400 nm von 10% oder weniger aufweist, wenn die Dicke des Glases 1,5 mm beträgt.
  8. Brillenglas nach Anspruch 1, welches eine Lichtdurchlässigkeit von 87% oder mehr aufweist, wenn die Dicke des Glases 1,5 mm beträgt.
  9. Brillenglas nach Anspruch 1, welches einen Gelbheitsindex (Yl) von 0,7 bis 1,8 aufweist, wenn die Dicke des Glases 5,0 mm beträgt.
  10. Brillenglas nach Anspruch 1, wobei der Ultraviolett-Absorber (A) mindestens einer ist, ausgewählt aus der Gruppe, welche aus 2-Hydroxy-4-methoxybenzophenon, 2-Hydroxy-4-n-octoxybenzophenon, 2-Hydroxy-4-methoxy-2'-carboxybenzophenon, 2,4-Di-hydroxybenzophenon, 2-(2'-Hydroxy-5'-methylphenyl)benzotriazol, 2-[2-Hydroxy-3-(3,4,5,6-tetrahydrophthalimidmethyl)-5-methylphenyl]benzotriazol, 2-(2-Hydroxy-3,5-di-tert.-butylphenyl)benzotriazol und 2-(2'-Hydroxy-5'-tert.-octylphenyl)benzotriazol besteht.
  11. Brillenglas nach Anspruch 1, wobei der Ultraviolett-Absorber (A) mindestens einer ist, ausgewählt aus der Gruppe, welche aus 2-(2'-Hydroxy-5'-methylphenyl)benzotriazol und 2-(2'-Hydroxy-5'-tert.-octylphenyl)benzotriazol besteht.
  12. Brillenglas nach Anspruch 1, wobei der Ultraviolett-Absorber (B) mindestens einer ist, ausgewählt aus der Gruppe, welche aus 2,2-Di-hydroxy-4-methoxybenzophenon, 2-(3-Tert.-butyl-5-methyl-2-hydroxyphenyl)-5-chlor-benzotriazol, 2-(3,5-Di-tert.-butyl-2-hydroxyphenyl)-5-chlorbenzotriazol, 2,2'-Methylenbis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazol-2-yl)phenol, 2-[2-Hydroxy-3,5-bis(α,α-dimethylbenzyl]-2H-benzotrialzol und 2-(3,5-Di-tert.-amyl-2-hydroxyphenyl)benzotriazol besteht.
  13. Brillenglas nach Anspruch 1, wobei der Ultraviolett-Absorber (B) mindestens einer ist, ausgewählt aus der Gruppe, welche aus 2-(3-Tert.-butyl-5-methyl-2-hydroxyphenyl)-5-chlorbenzotriazol, 2,2'-Methylenbis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazol-2-yl)phenyl] und 2-[2-Hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotrialzol, besteht.
  14. Brillenglas nach Anspruch 1, wobei das Polycarbonat-Harz 2,2-Bis(4-hydroxyphenyl)propan als hauptsächliche, zweiwertige Phenolkomponente umfaßt.
  15. Brillenglas, erzeugt aus einer Harzzusammensetzung, welche im wesentlichen zusammengesetzt ist aus:
    (1) 100 Gewichtsteilen eines Polycarbonat-Harzes; und
    (2) 0,5 bis 3 Gewichtsteilen eines Ultraviolett-Absorbers mit einem APHA-Wert von 200 oder weniger und einem Molekulargewicht von 500 bis 2.000 und welcher durch die folgende allgemeine Formel (1) dargestellt wird:
    Figure 00420001
    wobei X ein Wasserstoffatom, Halogenatom, Alkylgruppe, Arylgruppe, Aralkylgruppe, Alkoxygruppe, Aryloxygruppe oder Aralkyloxygruppe ist, R1 und R2 unabhängig voneinander eine Alkylgruppe oder Aralkylgruppe sind, und Y eine zweiwertige organische Gruppe zum Koppeln von zwei Benzotriazolylphenolgruppen ist.
  16. Brillenglas nach Anspruch 15, welches eine Spektraldurchlässigkeit für eine Wellenlänge von 400 nm von 10% oder weniger aufweist, wenn die Dicke des Glases 1,5 mm beträgt.
  17. Brillenglas nach Anspruch 15, welches eine Lichtdurchlässigkeit von 87% oder mehr aufweist, wenn die Dicke des Glases 1,5 mm beträgt.
  18. Brillenglas nach Anspruch 15, welches einen Gelbheitsindex (Yl) von 0,7 bis 1,8 aufweist, wenn die Dicke des Glases 5,0 mm beträgt.
  19. Brillenglas nach Anspruch 15, wobei der Ultraviolett-Absorber, welcher durch die vorstehende allgemeine Formel (1) dargestellt wird, mindestens einer ist, ausgewählt aus der Gruppe, welche aus 2,2-Methylenbis[4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazol-2-yl)phenol] und Hexan-1,6-diylbis[3-(3-benzotriazol-2-yl-5-tert.-butyl-4-hydroxyphenyl)propionat] besteht.
  20. Brillenglas nach Anspruch 15, wobei das Polycarbonat-Harz 2,2-Bis[4-hydroxyphenyl)propan als hauptsächliche, zweiwertige Phenolkomponente umfaßt.
EP19970300271 1996-01-26 1997-01-17 Brillenglas Revoked EP0786675B1 (de)

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US8691915B2 (en) 2012-04-23 2014-04-08 Sabic Innovative Plastics Ip B.V. Copolymers and polymer blends having improved refractive indices
US20210017359A1 (en) * 2016-11-28 2021-01-21 Mitsubishi Engineering-Plastics Corporation Polycarbonate resin composition
US20210024721A1 (en) * 2016-11-28 2021-01-28 Mitsubishi Engineering-Plastics Corporation Polycarbonate resin composition
US11608426B2 (en) * 2016-11-28 2023-03-21 Mitsubishi Engineering-Plastics Corporation Polycarbonate resin composition
US11613626B2 (en) * 2016-11-28 2023-03-28 Mitsubishi Engineering-Plastics Corporation Polycarbonate resin composition

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DE69716789D1 (de) 2002-12-12
EP0786675A2 (de) 1997-07-30
US5952096A (en) 1999-09-14
EP0786675A3 (de) 2000-03-01

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